xhost +local: && winecfg? I don't know if that is enough to get past the chroot. I just use a separate user cleverly named 'wine' and change the permissions on the executable so only that user can run wine programs.

EDIT: You need to run xhost before you chroot. Its in x11-apps/xhost if you don't already have it installed._________________First things first, but not necessarily in that order.